Custom Trip Planning with Jen Ahana
Custom Trip Planning with Jen Ahana

Most people visit the world's best places.
Few actually experience them.

Extraordinary trips don't happen. They're built.

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Watch Before You Book

See exactly how this works.

Four minutes. Everything you need to know about what goes into your plan — and what makes it different.

Ready to Go — Book Now

The Cost of Getting It Wrong

A $12,000 trip ruined by a $0 plan.

Wrong turns. Full parking lots at 7am. Trails that took three times longer than the blog said. A viewpoint closed for the season. These aren't worst-case scenarios — they're what happens when you navigate an unfamiliar destination with a generic itinerary written by someone who spent three days there.

For most people, this isn't a trip they do every year. They saved for it. They planned around it. They've been thinking about it for years. There's no do-over.

"The best trips in the world don't happen by chance. They're planned that way."

A travel agent hands you a template. A blog post gives you the same five stops everyone else visits. A quick Google search gives you a firehose of conflicting information that makes the planning feel harder — not easier.

What you actually need is someone who has been there. Not for a press trip. Not for a weekend. Someone who has spent enough time on the ground that they know which trail to take on a cloudy morning, where to park before dawn, and which "must-see" viewpoints are full of tour buses by 9am.

A Different Approach

A travel agent tells you
what to do.
I start by asking
what you want.

Every custom plan begins with understanding what this trip needs to be for you. Not what's trending. Not what everyone else books. What matters to you — the experiences you want to have, the way you want to move through a place, the story you'll still be telling ten years from now.

Once I understand that, everything else is designed around it. The route. The timing. The pace. Every decision is filtered through what's right for your specific trip — not a template, not a list.

You get a plan that is entirely, specifically yours.

How It Works

Three steps.
One extraordinary trip.

01

Trip Vision Intake

Before we speak, you'll complete a detailed intake about your dates, priorities, travel style, and what you want this trip to feel like. By the time we connect, I've already been immersed in your destination and your goals — so every minute of our call counts.

02

Private Strategy Call

A focused 60-minute session where we map out your trip together. We make the key decisions, resolve every open question, and land on a direction that feels right. You'll hang up with complete clarity — and a lot of anticipation for what's ahead.

03

Your Custom Playbook

Within 48 hours, I deliver your complete plan: a fully built day-by-day playbook (15+ pages, scaled to your trip) with your route, timing, insider notes, and a custom Google Earth map of every trail, stop, and key location. Open it. Step into it.

Everything Included

Built for a trip
worth remembering.

Before We Connect
Trip Vision Intake

A detailed pre-call questionnaire so I arrive on our call fully prepared — already immersed in your destination and your goals.

Live Session
60-Minute Private Strategy Call

Focused entirely on you. We work through the destination together — route, timing, questions, decisions — and land on a plan that fits how you travel.

The Deliverable
Custom Travel Playbook (15+ Pages)

Your complete, day-by-day plan. Specific, actionable, and designed around how you travel. Delivered within 48 hours of our call.

Navigation
Custom Google Earth Map

Every trail, every stop, every key location plotted and ready. Open it on arrival. Never wonder where you are or what's next.

Insider Intelligence
On-the-Ground Expertise

Not blogs. Not generic recommendations. Years of real time in real places — the details that transform a well-planned trip into one you'll talk about for a decade.

All in One Place
Every Resource Linked & Ready

Every recommendation, reference, and link organized and ready to use. No more tabs. No more searching. Open it and go.

Essential
Up to 5 Days
$750

A single-region itinerary, fully built. Every trail, town, and timing decision handled — designed around how you travel, not how everyone else does. Ideal for couples and solo travelers carving out one unforgettable week.

Signature
10–12 Days
$1250

A full immersion. Complex multi-region planning, deeper pacing, and the kind of itinerary built for trips you've been dreaming about for years. For groups and travelers who want the full reach of what's possible — and the plan you'll still be talking about a decade from now.

You're investing $10,000–$50,000+ in the trip itself.
This is the smallest line item — and the one that protects everything else.

Jen Ahana
Your Guide

Jen Ahana

Some people discover travel. I discovered I couldn't live without it — so I walked away from everything else and made it my life.

That's taken me across five of New Zealand's Great Walks, months deep into the Dolomites where I know the trails well enough to write the guidebook, through the raw Highlands of Iceland, and into the hidden corners of the American West.

When I show up for your consult, so does every trail, every summit, and every hard-earned lesson from five continents of exploration. You get all of that, applied directly to your trip.

Host & Executive Producer, Explore This — 1 million views & watching
Adobe Creator Award Winner — one of ten recognized globally
Author of Beyond the Ring Road: Hidden Gems of Iceland
Author of Dolomites 5-Day Itinerary & Beyond Cortina: Explore the Hidden Gems of the Eastern Dolomites
Author of The 90-Day Life: How to Live More in 3 Months Than You Have in 3 Years
Tourism board partner across Europe, Iceland & beyond
Client Experiences

Travelers who know what they want —
and found someone who could deliver it.

Shelley & David · Dolomites Anniversary Trip

Loren testimonial

Having an expert with true experience...made planning a complicated trip like this so helpful.

Loren · Italian Dolomites

Tom & Friends testimonial

All the fears have vanished and we are very confident we'll be going at a very special time.

Tom & Friends · Dolomites Off-Season

Solo traveler testimonial

Jen is truly interested in helping navigate the best travel experience.

Dolomites · Solo Trip

Before You Book

This isn't for everyone.
It's for you — if.

This isn't for the casual traveler who wants a quick list. This is for the person who has been dreaming about this trip for years. Who wants to experience a destination the right way. Who understands that the gap between a good trip and an extraordinary one is worth investing in.

I keep this circle small on purpose. Between producing my show and working with tourism boards worldwide, every person who books gets my full attention — my deepest knowledge, and everything I've learned across five continents. That's only possible when the list stays short.

"This isn't a volume business. It never will be."

If a spot is open when you're reading this, that's your window. Click below, land on a secure checkout page, and your spot is secured in about 30 seconds. The hard part — trying to figure all of this out yourself — is over.

The best part comes next.

This is the part where
you become one of the few.

Your destination is waiting. Your dates are set. The only thing missing is a plan worthy of the trip you've been building toward — and the person who can build it.

Build My Trip

Spots are limited. Secure yours in 30 seconds.

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Bell Ring

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